18. Bob Dylan
Band: Bob Dylan
Like his hero Woody Guthrie, Bob Dylan was a product of his country and sang as the voice of its people. But his style was pure New York City bohemian. A dark coolness pervaded through Dylan's style, giving the sense that there was always much more behind his deceivingly simple sounding lyrics. Emerging from the Manhattan's Greenwich Village in the 1960s, Dylan meteoric rise to fame saw his style hardly change. If somber black, belted coats, and hearty workwear is your thing and it's working for you, then it shouldn't matter what else is blowing in the wind.